Dicyclohexylcarbodiimide → Retinal

HRID 346880

Reaction equation

HRID 346880 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](O)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/CO>ClCCl.CCCCCC.C(OCC)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[CH:18]=[O:19]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 444795Retinoic AcidHCID 445354Retinol

Product 1

HCID 638015RetinalYield 129.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584099Diethylether hexaneSolvent

Procedure

Retinoic acid (1.26 g, 0.0042 mol, Basf Co.), dicyclohexylcarbodiimide (DCC) (0.87 g, 0.0042 mol) and catalytic amount of dimethylaminopyridine (DMAP) were added to retinol (1.00 g, 0.0035 mol) dissolved in anhydrous dichloromethane (50 ml) at 0° C. The reaction solution was slowly warmed to room temperature and stirred for 12 hours under nitrogen atmosphere and under the condition for light and moisture to be intercepted. The reaction solution was filtered and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (silica gel 60 for cc part, Merk Co., mesh size 270–400, hexane/diethylether=19/1, v/v) to give 1.55 g (Yield 78%) of the pale yellow title compound.

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 60 for cc part, Merk Co

Sources & evidence

ORD record
ord-9eb3a1f1fd5e4d55865230379739028c
Source dataset
uspto-grants-2007_02
Patent number
US07173062B2

Linked notes

Loading…